3 Shenandoah Valley Weekend Getaways Perfect for Fall

Explore the Virginia region’s history, nature and culture this season.


With the Blue Ridge Mountains to the east and the Alleghenies to the west, Virginia’s Shenandoah Valley is a leaf peeper’s paradise. Foliage peaks mid to late October, but the area is teeming with activity throughout the fall. Here are three itineraries to get you started.

Winchester-Frederick County


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Drive Time:

3 hours, 15 minutes.

Stay Here:

The Pembroke Springs Retreat

The Pembroke Springs Retreat transports guests to Asia with an authentic five-guestroom Japanese ryokan (inn) complete with two large, private onsen (warm mineral spring water baths), yakuda (robes) for lounging and a traditional Japanese breakfast. The 175 scenic acres boast three miles of natural trails, a private pond for fishing and an all-season tennis court. Time your visit to coincide with the renowned Asian-fusion dinners ($40 for three courses, $55 for four).

$250- $350. Two-night minimum on Fridays and Saturdays. 6238 Wardensville Grade, Star Tannery, Va., (540) 877-2600, www.pembrokesprings.com.

The Inn at Vaucluse Springs

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Choose from six different guest houses at the lovingly restored 1785 mansion house, a log and stone 1850s house, or one of six private cabins nestled on the Inn at Vaucluse Spring’s 44 acres. Some have fireplaces and Jacuzzis for two. Before tucking into the three-course breakfast, take a one-hour morning class that combines meditation, gentle yoga and mindful walking ($20 per guest).

$199-$349. 231 Vaucluse Spring Lane, Stephens City, Va., (540) 869-0200, www.vauclusespring.com.

The Inn at Valcluse Springs

Eat Here:

Sweet Nola’s

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After experiencing Asia and colonial America, get a taste of New Orleans at Sweet Nola’s, where eight different variations on the po’ boy
($16-$18.25) are offered. Wednesday nights feature authentic jambalaya and gumbolaya with sausage and chicken or seafood ($17.75-$20.75). Thursday, it’s shrimp and grits ($16.75). Stick around for a performance by the house jazz band every Wednesday evening and Saturday afternoon.

688 N. Loudoun St., Winchester, Va., (540) 667-6652, www.sweetnolas.com.

Aroma Deli

Don’t miss the Peruvian chicken at Aroma Deli. A meal for one includes a quarter of a chicken with choice of two sides like black beans, corn salad and plantains. Or opt for a family meal with a whole bird and three sides.

$7.50-$15.75. 201 E. Boscawen St., Winchester, Va., (540) 545-4627, www.aromadeliwinchester.com.

Crush Wine Bar

Order a glass, flight or bottle from a menu of over 100 international labels at Crush Wine Bar and pair with caviar selections that range from bowfin ($58) to Russian ostera ($125). Intriguing small plates include elk, goat cheese and red onion flatbread, escargot, candied smoked salmon and international cheese boards.

3031-103 Valley Ave., Winchester, Va., (540) 550-0103; www.thecrushwinebar.com.

To-Do List:

Belle Grove Plantation

Get a glimpse of antebellum life on a guided tour of Belle Grove Plantation, a 1797 manor house. Self-guided tours of the 19th-century outbuildings, slave cemetery, gardens and archaeological excavation are also available.

$12. 336 Belle Grove Road, Middletown, Va., (540) 869-2028, www.bellegrove.org.

Photo By Buddy Secor

Loudoun Street Mall

The two-block pedestrian-only Loudoun Street Mall in Old Town Winchester has 35 restaurants, more than 60 shops and boutiques, and numerous museums and historic houses. Stop at the George Washington Office Museum, housed in an 18th-century log-and-stone building. It tells the story of our first president through his personal effects and interactive exhibits.

$5. 32 W. Cork St., Winchester, Va., (540) 662-4412, www.winchesterhistory.org.

The Glen Burnie House

In the Glen Burnie House at the Museum of the Shenandoah Valley, you’ll find major collections of 18th- and 19th-century European and American fine and decorative arts. Be sure to visit the museum’s R. Lee Taylor Gallery with its miniature houses.

$12. 901 Amherst St., Winchester, Va., (540) 662-1473, www.themsv.org.

Shenandoah Valley Civil War Museum

A former courthouse, hospital, prison and military barracks, the Shenandoah Valley Civil War Museum showcases period relics, exhibits and more.

$5. 20 N. Loudoun St., Winchester, Va., (540) 542-1145, www.civilwarmuseum.org.

Free Music Afternoons

On the first and third Fridays of the month, enjoy an afternoon of free music featuring Shenandoah Conservatory faculty and students.

Winchester Medical Center North Tower Lobby, 1840 Amherst St., Winchester, Va., (540) 536-8000.

Explore Local Arts and Crafts

Upwards of 20 artists and crafters make up the Top of Virginia Artisan Trail.

(540) 886-1684, www.artisanscenterofvirginia.org.

Local artisans are also well represented at Berryville Treasures.

 8 W. Main St., Berryville, Va., (540) 955-4850.

Handworks Gallery

And be sure to make a stop at Handworks Gallery for fine local, regional and national Fair Trade handcrafts and global art. Their inventory includes jewelry, pottery, and fashion and home décor accessories.

150 N. Loudoun St., Winchester, Va., (540) 662-3927, www.handworks-gallery.com.

Fall-Themed Fun 

Revel in the season’s colors as you hike the 4.8-mile Biby Trail to Pinnacle Shelter on the Tuscarora Trail in George Washington National Forest.


Or travelthe scenic foothills and ridges on a horseback trail ride with Walking After Midnight Farm.

$40-$60. 225 Morgan Road, Cross Junction, Va., (540) 303-0569,www.walking-after-midnight.com.

More than 7,500 visitors flock to the Frederick County Fairgrounds for the annual Shenandoah Valley Apple Harvest Festival. This year’s event takes place Sept. 21-22 and will include apple-eating and pie-making contests, apple butter making, hard cider and beer tastings, a canine obstacle course, a human hamster ball, live entertainment, and a zone for kids.

$8. 250 Fairground Road, Clear Brook, Va., www.winchesterappleharvest.com.

Shenandoah County


Drive Time:

4 hours.

Stay Here:

The Jacob Swartz House

The two-bedroom, two-bathroom former cobbler’s shop at the Jacob Swartz House was built in 1852. The cottage sits on more than three landscaped acres overlooking the Shenandoah River and features a living room, a dining area, a kitchen and sunroom, a screened porch and terrace, and an electric fireplace. A full hot breakfast is brought to your cottage.

$150 double occupancy. 574 Jiggady Road, New Market, Va., (540) 740-9208, www.jacobswartz.com.

Eat Here:

Woodstock Garden Café

Find exceptional lunch fare amid the flowers, greenery and garden art for sale at Fort Valley Nursery’s Woodstock Garden Café. Be sure to try the Asian chicken with noodles tossed in homemade maple soy dressing and topped with mandarin oranges, toasted almonds and sesame seeds. Many of the ingredients come from the owners’ farm.

$6.95-$7.95. 1175 S. Hisey Ave., Woodstock, Va., (540) 459-5151, www.fortvalleynursery.com.

Woodstock Garden Cafe

Sal’s Italian Bistro

Create your perfect pasta at Sal’s Italian Bistro, which offers nine pastas and 20 sauces. The meat and seafood entrées are great, too.

$14-$25. 125 S. Main St., Edinburg, Va., (540) 984-9300, www.salsitalianbistro.com.

Hotel Strasburg

For a romantic candle-lit dinner, try the posh Victorian setting at the Hotel Strasburg. Start with shrimp and grits, then dive into the crab cakes or a pork loin with apples and bourbon.

$9-$22. 213 S. Holliday St., Strasburg, Va., (540) 465-9191, www.hotelstrasburg.com.

To-Do List

Shenandoah Wine Tours

Sip to your heart’s content at four of the area’s premier wineries—Muse, Wolf Gap, Cave Ridge and the Winery at Kindred Point—when you let Shenandoah Wine Tours do the driving.

$49-$59, plus tasting fees. 204 N. River Drive, Edinburg, Va., (540) 481-0762, www.shenandoahwinetours.com.

Bryce Resort Golf Course

At Bryce Resort, you can play 18 holes on a championship golf course, ride eight lift-assisted trails challenges, glide 90 feet above the ground on 11 different ziplines, or simply take in the majestic mountain views on a chair lift.

$8-$135. 982 Fairway Drive, Basye, Va., (540) 856-2121, www.bryceresort.com.

Bryce Resort Golf Course

New Market Battlefield

Known as the “Field of Lost Shoes” for the thick mud that claimed the shoes off soldiers’ feet, the New Market Battlefield and its museum tell the story of a corps of young cadets from the Virginia Military Institute involved in a May 1864 battle. On Oct. 26, Spirits of New Market guides visitors on a lantern-lit tour of the battlefield, complete with reenactors.

$7-$10. 8895 George Collins Pkwy., New Market, Va., (866) 515-1864, www.vmi.edu.      

Edinburg Mill Museum

Housed in one of the few mills to survive the Civil War, the Shenandoah Valley Cultural Heritage Museum at the Edinburg Mill offers three floors of displays filled with technology, transportation and memorabilia from the 19th and 20th centuries.

$3. 214 S. Main St., Edinburg, Va., (540) 984-8400, www.edinburgmill.com.

Shenandoah Museum of Contemporary Art

The Shenandoah Museum of Contemporary Art features a constantly changing array of dynamic and dramatic installations by some of today’s most innovative visionaries.

411 E. King St., Strasburg, Va., (540) 333-4252, www.shenmoca.org.

Fall-Themed Fun

 It’s a short hike and three stories up to the top of Woodstock Tower. There you’ll find a 360-degree view of the town, surrounding area and seven bends of the Shenandoah River.

Woodstock Tower Road, Woodstock, Va., (540) 459-6227, www.virginia.org.

View overlooking the Shenandoah River. 


Get a bird’s-eye view of the valley’s autumnal splendor while drifting through the air on a tandem dive with Skydive Shenandoah.

$225. 57 River Road, New Market, Va., (540) 740-9312, www.skydiveshenandoah.com.

Or soar above the treetops during sunrise or sunset with Valley Ballooning.

$220 per person. 16350 Old Valley Pike, Edinburg, Va., (540) 975-0192, www.valleyballooning.com.

Photo by Katie Rudolph


Sept. 13-Oct. 13, watch live harness racing from the grandstand every Friday and Saturday at Shenandoah Downs. Admission is free and you can bet on most races.

Shenandoah Fairgrounds, 300 Fairground Road, Woodstock, Va., (540) 459-3867, www.shenandoahdowns.com.



Drive Time:

4 hours, 45 minutes.

Stay Here:

Iris Inn

Situated on a 12-acre Blue Ridge mountaintop overlooking the rolling farmland of the Shenandoah Valley, the Iris Inn offers a warm welcome in luxurious surroundings. Stay in the main house or a private glass-fronted cabin or cottage. Cottages have efficiency kitchens, fireplaces and two-person showers with body jets. Cabins offer full kitchens, personal washers and dryers, rain-head showers and hot tubs. Breakfast and complimentary wine and cheese are included.

$159-$499. 191 Chinquapin Drive, Waynesboro, Va., (540) 943-1991, www.irisinn.com.

Eat here: 

Stella, Bella & Lucy’s

Founded by two artists and named for their beloved dogs, Stella, Bella & Lucy’s dishes up homemade Southern cuisine for breakfast and lunch in an art-filled dining room. Try the Granny sandwich, with corned beef and house-made pimento cheese or the Carolina barbecue on grilled challah bread. Save room for the house-made desserts.

$7.75-$9.50. 327 W. Main St., Waynesboro, Va., (540) 949-5111, www.stellabellalucy.com.

Stella, Bella & Lucy’s

Heritage on Main Street

Featuring a contemporary upscale menu and atmosphere, Heritage on Main Street offers creative entrées like fall foliage pork tenderloin with a ginger molasses cookie breading and blueberry demi-glace. Just a couple blocks from the Wayne Theatre, it’s the perfect spot for a pre-performance meal.

Heritage on Main Street

$15-$27. 309 W. Main St., Waynesboro, Va., (540) 946-6166, www.heritageonmainstreet.com.

Green Leaf Grill

Shrimp-stuffed hush puppies and fried alligator are among the starters at Green Leaf Grill. For a main course, try the crab-and-chicken gumbo.

$15-$24. 415 W. Main St., Waynesboro, Va., (540) 949-4416, www.thegreenleafgrill.com.

To-Do List

South River Fly Shop

Try your hand at fly fishing on a guided tour with South River Fly Shop. $225-$325. 323 W. Main St., Waynesboro, Va., (540) 942-5566, www.southriverflyshop.com.

Frontier Culture Museum

At the Frontier Culture Museum, learn about the lives of early immigrants by wandering among the reproduction buildings from England, Germany, Ireland and West Africa.

$12. 1290 Richmond Ave., Staunton, Va., (540) 332-7850, www.frontiermuseum.org.

P. Buckley Moss Gallery

Discover the work of nationally renowned artist P. Buckley Moss at her eponymous gallery in Waynesboro.

329 W. Main St., Waynesboro, Va., (540) 949-6473, www.pbuckleymoss.com.

Shenandoah Beerwerks Trail

On the Shenandoah Beerwerks Trail, you’ll be chauffeured to tastings at three Waynesboro breweries—Basic City Beer Co., Stable Craft Brewing and Seven Arrows Brewing Company. $69. www.beerwerkstrail.com.

Blue Ridge Bucha

If something a little healthier is up your alley, pay a visit to Blue Ridge Bucha, which makes Certified Organic fruit- and flower-infused kambucha and fermented tea, including a Brewcha with coffee and a Kombu-Chai with tea.

1809 E. Main St., Wayneboro, Va., (540) 221-6500, www.blueridgebucha.com.

Fall-Themed Fun

First opened as a vaudeville house in 1926, the beautifully restored Wayne Theatre offers everything from music and dance to Broadway productions. See The Return: A Tribute to the Beatles on Oct. 10, the U.S. Army Jazz Ambassadors on Oct. 16 and Death Trap Oct. 17-26.

521 W. Main St., Waynesboro, Va., (540) 943-9999, www.waynetheatre.org.

Twelve talented artists—including painters, a metal sculptor and etched silver jewelry- and pottery-makers—work in the open studios at the Shenandoah Valley Art Center. The gift shop is a treasure trove of local and regional art. The center also produces the Virginia Fall Foliage Art Show, which features 150 juried

local and regional fine artists, along with music, gourmet food trucks and regional craft beer. This year’s event runs Oct. 12-13.

126 S. Wayne Ave., Waynesboro, Va., (540) 949-7662, www.svacart.com.

Each fall, more than 20,000 raptors—including hawks, falcons, eagles and osprey—migrate through Rockfish Gap Hawk Watch. Peak migration times are the last two weeks in September and the first two weeks in October. The viewing site is easily accessible, with no hiking required.

On the grounds of Inn at Afton, 185 Afton Circle, Afton, Va., www.rockfishgaphawkwatch.org


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